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. 2019 Sep 12;9(49):28718–28723. doi: 10.1039/c9ra05748j

HS-cellulose sulfate catalyzed synthesis of dihydroquinazolinones derivatives in water.

Entrya R1 R2 Pro Time (h) Yieldb (%)
1 –C6H5 H 3a 0.7 94 (90, 88, 82)c
2 4-CH3–C6H4 H 3b 1.5 87
3d 4-N(CH3)2–C6H4 H 3c 1.5 98
4 4-OCH3–C6H4 H 3d 1.0 86
5 4-NO2–C6H4 H 3e 1.0 87
6 4-COOH–C6H4 H 3f 2.0 91
7d 4-C6H5–C6H4 H 3g 2.0 80
8 4-F–C6H4 H 3h 1.0 89
9d 4-Br–C6H4 H 3i 1.5 85
10d 4-Cl–C6H4 H 3j 1.5 92
11 2-Cl–C6H4 H 3k 2.0 98
12 3-Cl–C6H4 H 3l 2.0 83
13 4-OH–3-OCH3–C6H4 H 3m 1.0 95
14 –C4H3S H 3n 2.0 88
15 –C6H5 4-NO2 3o 1.5 91
16 4-CH3–C6H5 4-NO2 3p 1.5 90
17 4-Cl–C6H5 4-NO2 3q 1.5 89
18 2-Cl–C6H5 4-NO2 3r 2.0 92
19 –C6H5 5-Cl 3s 6.0 N.R
20 –C6H5 5-OCH3 3t 6.0 Trace
a

Reaction conditions: aromatic aldehyde (0.5 mmol), aminobenzamide (0.5 mmol), HS-cellulose sulphate (10 mg), 60 °C; water (1.5 mL). The reactions were run until completion as indicated by TLC. N.R: no reaction. All the compounds are known, characterized by 1H NMR and 13C NMR.

b

Isolated yield.

c

The recovered catalyst cycle yield.

d

The solvent was water : ethanol = 1 : 1.